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DOI: 10.1055/s-0030-1258224
Reactions of Substituted Oxazoles and Thiazoles with Acid Chlorides: Carbon-Carbon Bond Formation through Cyclic Ketene Acetals
Publication History
Publication Date:
20 August 2010 (online)
Abstract
Reactions of 2,4,5-trimethyloxazole, 2,4,5-trimethylthiazole, 2-methylthiazole, and 2-ethyl-4,5-dimethylthiazole with different acid chlorides in the presence of different bases were explored. Arylvinyl esters of substituted benzoic acids containing substituted oxazoles or thiazoles were formed when aroyl chlorides were used. Degrees of aroylation were different with different bases. Reactions with alkyl acid chlorides were also explored. Most of these reactions occurred through cyclic ketene acetal intermediates.
Key words
carbon-carbon bond formation - oxazoles - thiazoles - vinyl esters - in situ generated cyclic ketene acetal
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References
CCDC 765577 (3d), 765578 (4d), and 765826 (9a) contain the supplementary crystallographic data for this paper. These data can be obtained free of charge from The Cambridge Crystallographic Data Centre via www.ccdc.cam.ac.uk/data_request/cif.